The itinerary below is centered around doing the Kentucky Bourbon Trail with a couple of other stops along the way including Mammoth Caves, The Natural Bridge, and Churchill Downs (where the Kentucky Derby is held in May). You will have to check the schedule for see if any horse races are happening at Churchill Downs, though, or they also have tours. My friend who is from Kentucky suggested most of the places we went to and we also drove from Maryland to Kentucky, which took about 8 hours. We went to 10 distilleries (Town Branch, Woodford Reserve, Castle and Key, Jim Beam, Rabbit Hole, Bulleit, Evan Williams, Old Forester, Makers Mark, and Four Roses), opting to do a tour at all except Old Forester and Four Roses. I swapped out Rabbit Hole and Town Branch with Angels Envy and Buffalo Trace on the itinerary because they would probably be better ones to visit. If you are trying to visit distilleries only, you could probably spend 2-3 full days or a weekend doing the tours and tastings. Definitely make reservations ahead of time, though, because most of the tours sell out. I’ll make a blog post later detailing all the tours and which were the best/had the best bourbon.
Day 1
Wake up at Natural Bridge State Resort Park
Take the Skylift to the Natural Bridge and hike around park
Drive to Chimney Top Rock in the Daniel Boone National Forest (the overlook is a 5 minute walk)
Drive to Buffalo Trace for Distillery Tour (hour and a half drive)
Dinner at The Kentucky Castle
Stay at Guesthouse Inn and Suites (Lexington)
Day 2
Woodford Reserve Distillery Tour
Castle and Key Tour
Jim Beam Tour (lunch at the restaurant onsite)
Tasting at Angel’s Envy in downtown Louisville
Stay at La Quinta (Louisville)
Day 3
Bulleit Distillery Tour
Churchill Downs for horse races
Lunch at J Grahams Café
Evan Williams Distillery Tour
Tasting at Old Forester Distillery
Day 4
Makers Mark Distillery Tour
Drive to Mammoth Cave (hour and a half drive from Louisville)
Mammoth Cave Tour (we did Dripstones and Domes because the Lantern one we wanted was sold out)
Stay at Mammoth Cave Lodge
Day 5
Stop at Four Roses Distillery and/or Wild Turkey for a tasting and drive home
